5-Nitroindazole → 1H-Indazol-5-amine

HRID 2386589Notes

Reaction equation

HRID 2386589 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[CH:7]2)([O-])=O>O1CCCC1.[Pd]>[NH:9]1[C:10]2[C:6](=[CH:5][C:4]([NH2:1])=[CH:12][CH:11]=2)[CH:7]=[N:8]1

Participants

4

Reactant 1

HCID 215015-Nitroindazole

Product 1

HCID 880121H-Indazol-5-amineYield 103.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a 5000 mL autolcave equipped with a H2 inlet, a thermometer, and a mechanical stirrer is added a solution of 5-nitro-1H-indazole (500 g, 3.06 mol) in tetrahydrofuran (THF, 3500 mL), followed by palladium on carbon (10%, 50 g, 141 mmol). The resulting mixture is stirred overnight at 25° C. under H2 atmosphere (5 kg pressure). After it is purged with N2, the mixture is filtered, and the filtrate is concentrated under vacuum to give the title compound (420 g, 100%) as a brown solid. MS (m/z): 134.1 (M+H).

Workup

  1. customTo a 5000 mL autolcave equipped with a H2 inlet
  2. customAfter it is purged with N2
  3. filtrationthe mixture is filtered
  4. concentrationthe filtrate is concentrated under vacuum

Sources & evidence

ORD record
ord-3f09ce27da2a4d959da6a8ad7a394803
Source dataset
uspto-grants-2012_09
Patent number
US08268836B2

Reaction notes

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